


Make Your Move

by Lavendermagik



Category: Supernatural
Genre: F/M, POV Second Person, Reader-Insert
Language: English
Status: Completed
Published: 2019-05-06
Updated: 2019-11-22
Packaged: 2020-02-26 22:39:24
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 9,387
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18726280
Author URL: https://archiveofourown.org/users/Lavendermagik/pseuds/Lavendermagik
Summary: You're newly single, and Dean is finally ready to make his move.  Seriously, he's going to do it.  Definitely.  Eventually.





	1. Chapter 1

“I got someone pregnant.”

Well, that’s not what you want to hear from the guy you thought was going to be your boyfriend.

“…oh?”

“It wasn’t planned. We weren't even serious, but now there's a baby involved, so…”

He trailed off expectantly. You weren’t sure exactly what that expectation was.

“I thought…” you began slowly, trying to give your mind time to catch up to the information influx. “I thought you couldn’t start a relationship until your ex-girlfriend settled down.”

It's what he'd told you, all those nights you'd shared a beer and talked about the two of you getting together. He wanted to, really wanted to, but his ex wasn’t handling their break up well, even after all these months, and he didn’t want that interfering with your relationship. As soon as she was sorted out… as soon…

“That's why the thing with this girl wasn’t supposed to be serious. But now the baby…”

He was repeating himself. You must be missing your lines.

“But-"

“You can’t expect me to abandon my kid!”

Oh. He was waiting for you to say the words that would officially end this pre-relationship or whatever it was and let him off the hook.

“I don’t expect anything from you. I’m just surprised, that's all.”

“You and me both.” He sighed deeply and rubbed a hand over his face. Then, apparently fortified, he reached for your hand and squeezed. “Look, you're great, amazing. I’m sorry this didn’t work out.”

“Right.” Your reply was short, but your tone was unaffected, agreeable even.

“Good things are going to happen for you.”

“Uh huh.” Very agreeable. 

“Really good things. Another guy, the right guy, is going to come along and snap you up in an instant.”

“Yeah, of course, thanks.” Inappropriately agreeable, given the circumstances. 

He left, and you sat in your motel room, pondering. You should be upset, right? Maybe mad? You'd been carrying around the idea of that guy being your boyfriend for close to six months – that was half a year! That was longer than Kim Kardashian’s first marriage. Sure, you'd never actually done anything. You'd never even had an official date. But you'd text each other most nights, and he'd brought you flowers after your last hunt had gone so well. He'd said he had feelings for you. You'd thought you'd had feelings for him. 

So where was the anger? The disappointment? Any emotion, really?

This right here was why you were single. You never reacted to things the way you were supposed to. Broken heart? Shrug. Snapped femur? Wrap it up. Dead body? That’s an unusually clean entry wound. Sure, guys talked about how much they hated emotional women, but present them with the other end of the spectrum and they ran for the hills.

Your unwavering calm may make you a good hunter, but apparently apathy was wildly unsexy. 

Well, you weren’t getting a boyfriend tonight. Might as well get a drink.

Consistency wasn’t something you normally get in the life you led, so that bars are the same pretty much everywhere was a blessing. The bartender might have tried flirting to see if he could wrangle a bigger tip out of you, but he let it go pretty quickly when your response was decidedly less than encouraging. Still, you couldn’t find it in yourself to be upset. You were just… here.

“Well, look what we have here.”

The voice was familiar even as unexpected as it was, so you were smiling even before you turned towards its owner. “Dean Winchester, as I live and breathe.”

“Glad to see you're still doing both.” His hug was warm and tight, and more welcome than you would have thought. Maybe you were more touch starved than you realized. “What's a girl like you doing in a place like this?”

“Vengeful spirit,” you announced, pulling back so you could see his face, and then spotted the other giant of a man behind him. “Sam!”

“Hey!” He caught you easily as you leapt off the stool to get your arms around him. “Didn’t expect to find you here."

“Right back at you. Last I heard you boys were up north somewhere.”

“Last we heard you were on the east coast.”

“Looks like all our info is old.” 

“So, vengeful spirit, huh?” Dean gestured to the bartender with two fingers before looking at back at you.

“Yeah, but don’t worry – I dusted the sucker earlier.”

“Guess that means we got the night off. Care to join us?”

“I thought you’d never ask.”

You relocated to a booth for more privacy before Sam indicated the drink in your hand and asked, “If the hunt went so well, what's with the hard stuff?”

“Oh,” you moved your shoulders enough that it probably counted as a shrug, “I figured it's what you're supposed to get when you’ve just been dumped.”

“You got dumped?” Dean's incredulity was so genuine you had to take it as a compliment. 

“I guess? Maybe that's not the right word for it if you were never really together.”

“What happened?”

“The guy I was supposed to want to like got another girl pregnant.”

A beat of silence passed before Sam asked with eyebrows rising, “Supposed to want to?”

“Yeah, I mean…” you spun your tumbler between you palms distractedly, “we'd talked about being a couple a lot. But he was having issues with his ex-girlfriend, and I didn’t mind waiting, but then today he tells me he's having a baby with someone else.”

“You don’t seem very upset about it,” Sam observed mildly, his face open and kind.

“I guess I’m not? I don’t know. I feel like I should be, but…” You didn’t know but what, so you just waved a hand to swat the hanging sentence away.

“Sounds like maybe you didn’t really like him all that much after all.”

“I thought I did, but you’re probably right.” You tossed back the end of your drink and regarded him with a raised eyebrow. “I thought you studied to be a lawyer, not a therapist.”

Sam smiled. “The two aren’t so far apart. They’re both about understanding human behavior.”

“Okay, enough of this sappy crap,” Dean broke in. “The guy is obviously a dick.

“Actually, he was pretty nice.” Your musing was more detached than the timespan should allow. “He brought me flowers and would ask how my day was and then actually listen to my answer. He was a hunter, but not obsessively so."

“What's that supposed to mean?” Dean bristled like you'd followed it up with ‘unlike _some_ people’, and you had to fight not to smack him.

“Nothing, put your quills back down. It was just nice that he could talk about something other than silver bullets and salt rings. You know, since that's not something _I'm_ very good at?” You, unfortunately, had few interests that didn’t involve shooting and/or stabbing.

“Doesn’t matter, he's still a dick. You don’t lead someone on like that.”

“Didn’t you just tell a woman a couple nights ago that you were a talent scout for a movie production company?” Sam's pointed question and look made you choke on a suppressed giggle.

“That’s not the same!” Dean looked utterly betrayed and turned his glare to his treacherous brother.

“You told her you could get her a role in the next Transformers movie.”

“I never said Transformers.”

“You said, quote, ‘Three words: robots in disguise.’”

Your sides were beginning to ache with your silent laughter. “He's right, Sam. It's not the same. If a girl is desperate enough to fall for that line, the fault is just as much on her. Though I guess the same could be argued for me.”

“No, you knew this guy.” Sam was quick to jump to your defense. “You thought you could trust him.”

“And he turned out to be a dick! So forget about him. You're single, you're hot, and you sent a vengeful spirit packing all on your own. His loss is our gain, but for some reason I only have one beer under my belt. Time to get this party started.”

Sam rolled his eyes, but you couldn’t stop your smile. “Let me see what I can do about that one beer. Next round is on me.”

Dean whooped as you stood and headed back for the bar. His eyes lingered until Sam nudged his arm sharply. “Dude.” 

Dean barely spared him a glance before looking back to where you'd leaned over the bar to get the bartender's attention. “I’m gonna go for it.”

“Come on man. We're actually on good terms with her. Why would you want to screw that up?”

“Shut up, Sam.”

“Seriously, she's fresh off a bad relationship. Do you really want to take advantage of her like that?”

“You bet your sweet ass I do.” Dean was launching himself from the booth before Sam could stop him. Ignoring his brother's warning calls he sauntered over to lean against the bar beside you. Your eyes caught his and you smiled. “Hi, my name is Dean, and I happen to be a talent scout for a movie production company.”

“Oh really?”

“Oh yeah, and I never do this, but I saw you standing here and knew you would be perfect for our next big movie. Three words: earth's mightiest heroes.”

You laughed so abruptly you snorted and slapped a hand over your mouth. Breathing deeply, you took in Dean's grin and crinkled eyes and shook your head. “Does that really work?”

“A lot of the time, yeah.”

“I’ve never been so disappointed in so many people simultaneously.”

“Why? What's your go to line?”

You snorted again, but this time without humor. “Hi, I’m sad and lonely?”

“Are you?” He was beginning to feel a little niggling of concern. “Sad and lonely?”

“No,” you sighed after a moment's contemplation, “mostly I'm just tired.”

Maybe tonight wasn't the best time to go for it after all.

Then you surprised him with a genuinely happy and dare-he-say-fond smile. “I’m glad you showed up tonight.”

This was promising. “Yeah?”

“Yeah. I’m obviously not too broken up over this whole thing, but I think I was really missing having friends around, you know? I’m really grateful that you’re here.” You were ostentatiously sincere, and Dean had never felt so dejected and pleased at the same time. Then you grabbed the necks of three bottles that had magically appeared in front of you. “Because now you can carry these back to Sam while I take a quick trip to the ladies' room.”

He watched you sashay away with that strange mixture of emotions simmering inside him. He returned to the booth to find his brother already smirking. “What happened to going for it?”

“She said she's glad to have friends around.”

“Oh, like someone who just went through a bad break up and could use some support instead of an immediate proposition?”

“Shut up, Sammy.”

“Look, man, you’ve had it bad for her for years now. What's another couple of days?”

“I thought you were worried about me screwing up our good terms,” Dean grumbled as he slouched over his beer.

“I am. So don't.” Sam's voice held a clear warning, which Dean respected but also kind of made him want to punch his baby brother in the face.

“What are we talking about?” You slid into the booth so suddenly that Dean almost dropped his beer.

“I thought you were going to the bathroom.”

“There was a line.”

“Hey, where are you headed after this?” Sam decided to mercifully save Dean from further embarrassment.

“I don’t know. I haven’t caught wind of anything else yet.”

“You should come back with us,” Dean blurted, and then would have blushed if he wasn’t too manly for such blood relocation.

“To your Batcave?” You didn’t seem to see anything unusual in Dean's behavior, for which he was grateful. “I don’t think so. It probably smells like boy.”

“What, like you smell like a bed of roses all the time?” 

You abruptly shoved your wrist under his nose. “That's actually the name of my perfume.”

You did in fact smell like roses. And vanilla? Well, that's distracting. 

“Come on, I’m sure the bunker smells fine.”

“It's called a bunker, so I find that hard to believe.”

“You could check out our library,” Sam cut it. “It's extensive.”

Why hadn’t Dean thought of that? Of course, ply her with books!

“Careful there, Winchester. You might never get rid of me.”

“Like that would be so bad,” Dean mumbled, then swallowed a too big mouthful when you looked at him strangely. 

“Okay, you got me. I'll check out your Batcave.”

“Awesome! I mean… yeah, it'll be fun. Our bunker es su bunker.”

“Gracias, mi amigo.”

Amigo. Okay, not ideal, but now you were going to be living with them. He'd have plenty of opportunities to make his move. He could do amigo for now.


	2. Chapter 2

Dean wished he’d made his bed, but then you sat on it and he decided he kind of liked the image better this way.

“What is this? It's all… cushy,” you asked as you pressed a palm into the mattress with fascination.

“Memory foam.”

“Oh, so it remembers you?” You smiled as you wiggled your whole body to further test the surface’s give.

He cleared his throat and returned a rather lame, “Yeah,” because you'd made his joke and that was weirdly hot.

“So I've been thinking,” you began, seemingly unaware of his struggles. He wondered if you’d been thinking the same things he’d been thinking, rumpled bedsheets and all, and if he should lock the door. “I don’t think I'm a lesbian.”

Well, that was unexpected. You'd been at the bunker for a couple days, and while he hadn’t officially made his move, he had been dropping some pretty heavy hints. He thought if you weren’t there to enthusiastically take him up on his offers at least you would demand he knock it off. Apparently, you had an entirely unrelated topic in mind.

“Don’t get me wrong – women are fine,” you continued. “They're great. I’m just not attracted to them, you know, sexually.”

Yeah, he knew being sexually attracted to women.

“And I don’t think I’m asexual either, because I _am_ sexually attracted to men. Sex with men is great.”

Good to know.

“So if I’m not a lesbian and I’m not asexual, what exactly is wrong with me?”

Oh, he should talk now. “What are you talking about?”

“My ex… something. Ex-almost-boyfriend?”

“The douche who got some other girl pregnant.”

“Yeah, so he posted a pregnancy announcement, and I thought, ‘Okay, here it is. Now I’ll be upset.’ But I got nothing. I couldn’t care less if he'd said he'd had eggs for breakfast. Actually, I might care more about that because I never did like the way he cooked eggs.”

“So what?” Dean didn’t really want to talk about a guy you used to be interested in. He'd rather talk about guys you might be interested in now. One guy. One guy who was wondering if it was weird that he was still standing by the door. “The guy is a dick. Why do you care whether or not you care?”

“Because I should, shouldn't I? Care? I wanted to date the guy and now he's happily starting a family with someone else. Shouldn't I have some kind of feelings about it? What if there's something wrong with me? What if I’m some kind of emotional wasteland where feelings go to die and that's why he wouldn’t commit?”

“Woah, slow down. You're not an emotional wasteland.” He finally decided to move away from the door and sit next to you. “Him being a tool has nothing to do with you. Remember what Sam said? If you’re not upset, then you must not have liked him all that much in the first place.”

“I thought I did.” You'd pulled one of his blankets over your lap and now ran your thumb back and forth over a seam. He covered your hand with his own, stilling its movement and bringing your eyes to his.

“Obviously, your subconscious mind knew you deserved better.”

You quirked an eyebrow. “Obviously, huh?”

“Hey, it's obvious to me. I still don’t know why you won’t admit that he's a douche.”

“Because he's _not_.”

“ _Obviously_ , he is.”

“No, he just ended up not wanting me like I thought he did.”

“Then he's a stupid douche.”

“You have got to stop saying douche.”

“Not until you agree he was one.”

“I’m not going to do that.”

“He's a douche. A big ol' douche.”

“Knock it off.”

“King of the douches.”

“You're a child.”

“The grand duke of douchebaggery.”

“You actually went down a step there, but nice alliteration.”

“Douche-canoe, douchebaggiest of all the douchebags, a prime example-" his list was cut off by your free hand slapping over his mouth. Which made him acknowledge that he was still holding on to your other one.

“Okay, I get it, you know all the variations of this particular insult. And if it makes you feel better,” you sighed and rolled your eyes, but let your hand drop. “Sleeping with another girl without telling me was pretty skeezy, so I suppose in this instance he could be considered a pretty massive douche.”

Dean grinned. “Feel better?”

“I wasn’t feeling bad to begin with – that was the problem, remember?” You shook your head, but your lips pulled up to mirror his. “But you did take my mind off that particular problem, so thank you.”

“Anytime.” Okay, you were in a good mood, in his bed, and he was still holding your hand. Prime time had arrived. “Hey, speaking of thinking-"

“Dean, I think I found something up in Minnesota. Five maulings with all organs removed except the heart.” Sam looked up from his laptop, one hand still on the doorknob, and glanced between you and Dean. “Uh, sorry, didn’t mean to interrupt.”

Dean knew he should have locked the door.

“Wait, all the organs _except_ the heart?” You were up and across the room in an instant; no embarrassment, like you hadn’t even heard Sam. Like what the situation could look like never even occurred to you. “What is that, like, some kind of reverse werewolf?”

“I don’t know yet,” Sam shot a questioning look at Dean over your head as you bent towards his computer. “I just found the article.”

“Wow, that’s some really graphic detail. I'll start checking into things that like to chow down on organs.” You slid past Sam and disappeared down the hall, mind already buried in the hunt. Sam leaned out the door to watch you go, and then looked back at Dean with raised eyebrows.

“Dude,” Dean was sure his glare could melt concrete as his hand clenched around the rapidly cooling blanket underneath it, “learn to knock.”


	3. Chapter 3

“You know your network makes no sense, right?” your voice echoed slightly from inside the small space. “Literally nothing in this place should function. This has got to be more magic than science.”

Dean wasn’t really listening, however. A few minutes prior you'd pulled off the front of a computer panel to inspect the wiring. Slowly you crawled further and further in until only the bottom half of your body stuck out.

And what a bottom it was.

“I mean, seriously, I know this place is super old, but you get internet and your map table lights up because of angels and stuff. There should be some cohesive structure in here somewhere.”

“How do you know so much about computers anyway?”

“I once spent an exorbitant amount of time with a computer programmer.”

“Ex-boyfriend?” Dean asked and then winced. That was an obviously specific question. 

“Ex-career path.” You didn’t seem to pick up on his social fumbling. You never did. “I did an internship right after high school, though in practice I was more of an administrative assistant than budding protégé. Either way it didn't work out. Not many monsters in hard drives.”

“We fought a vengeful spirit traveling by Wi-Fi once.”

“You fought a what?” You pulled back until you could see him, brow furrowed under a streak of dust.

“Internet ghost.”

“Ah. Sweet.” And then you were even further in than before.

A couple weeks had passed, and you hadn’t mentioned leaving yet, much to Dean's pleasure. He still hadn’t found the right time to ask you out, but even so he enjoyed your company. Maybe Sam was right – maybe he should just leave well enough alone. You were an awesome friend, so why mess with that?

He watched the muscles in your legs shift as you stretched and knew why.

You'd been picking through their library like a kid in a candy store, and it was frankly adorable. Today you'd decided to take a break and explore their network hookups, which were either amazing or ridiculous, maybe both. Between his ignorance on the subject and distraction due to your positioning, he was really only following about a third of what you said.

Even better, you hadn’t mentioned your breakup since that night in his room. You must be getting over it, which meant the time was ripe for Dean to swing in and grab the prize.

“Hey, there's been something I’ve been meaning to ask since we ran into you. For longer than that, actually. I've never brought it up because we always seem to be passing each other, like ships in the night or whatever. I didn’t want to start something with you if we couldn’t see it through, you know? I care about you too much, and Sam does, too. He threatened me, told me not to screw this up… which I think I might be doing, geez, sorry. Look, what I’m trying to say is do you wanna go to dinner?”

You ducked out and sat back on your heels, face alarmingly blank. “What did you say?”

“Dinner. Do you wanna go?” He was starting to sweat a little now. He'd finally sacked up and done it, and now he just had to wait for you to put him out of his misery. Would you say no? Had he said too much? Would you be uncomfortable around him now that he had spilled his guts?

“Sure,” you smiled at him as you pulled to your feet. “Sorry, it's hard to hear in there. Just let me go get changed – that thing is filthy.”

“Really?” Dean was having a hard time believing after everything it had been this easy. Had you really said yes to a date with him, just like that?

“Yeah, your housekeeping staff is terrible. What were you thinking for dinner?”

“Uh,” he really should have thought this out more, “I don’t know. What are you in the mood for?”

“Mm, same. Maybe Sam will have an opinion.”

“Sam?”

You wanted to ask Sam for date recommendations?

“Yeah, probably should have started with him. He has more dietary restrictions than either of us.”

“Sam,” Dean repeated, a terrible suspicion starting to worm its way into his head.

“I know they're self-imposed, but you can’t fault a guy for wanting to be healthier. But maybe he'll just be happy to be away from the bunker. We haven't had a night out since I got here. And I was right – this place does smell like boys. I'll meet you out front in ten.”

He could feel himself physically deflating as he watched you walk out brushing at your hair to shake free anything acquired during your adventure. Next time he was going to have to be a lot more specific. And maybe get rid of Sam for a week.


	4. Chapter 4

The problem was simple, Dean decided. What was really tripping him up was the actual words that he had to string together in order to ask you out. He always took too long or said the wrong thing. He needed to have it all laid out ahead of time so he couldn’t screw it up when the moment came.

He needed to write you a note.

Okay, so it was kind of a wuss move, but in his defense he'd missed out on a lot of the note passing in school. He deserved the tap out at least once.

The idea struck him on the way back from a food run, and he immediately pulled to a stop about a mile out from the bunker to rummage for the appropriate materials. You'd had a craving for a specific sandwich but also hadn’t wanted to put down your latest find from the library. Since he wasn’t making progress with you in any other arena, he might as well make all your gastronomical dreams come true. But what had started as a mere errand would now be a gateway to getting exactly what he wanted. If only he could find something to write on!

He settled for a napkin from one of the take out bags. The coarse brown material wasn’t ideal, but the blue pen he found in the glove box was legible enough. He slipped his note into the bag containing your food, and then put Baby back into gear with new purpose. This time would work – there was no way you'd misunderstand his intention.

He tried to walk normally into the library, but he was pretty sure even thinking about the way he walked was throwing off his stride. Sam gave him a patented ‘look', but you were so involved in your book that you barely acknowledged his entrance. 

“Here you go, sweetheart – dinner of champions.” He set your bag and requested drink near your arm.

“Thanks, Dean. You’re the best,” you answered without looking up.

“Uh, you probably want to get started on that. Don’t want to let it… sit too long.” See, this was why he had to write things out. His speaking words were not doing too good. His encouragement had the desired effect, at least initially. You reached out towards the bag, and he steeled himself for the moment you would discover his written invitation. Unfortunately, your eyes were still scanning the text before you, so you didn’t notice that instead of the bag of food you were headed for the cup. Your hand knocked into it with enough force to send it tumbling. The flimsy top popped right off and liquid spewed forth across the table.

You'd only asked for a small, so the mess wasn’t as big as it could have been. Still, it was enough to have you launching to your feet in panic. You ripped out the handful of napkins sitting in the mouth of your bag and frantically began sopping up the puddle. It all happened so quickly that Dean had a minute or so of leftover anticipation before the reality sank in. Amidst the clump in your hand he could see one napkin stained blue with running ink no longer forming anything remotely resembling words.

“I am so sorry, guys! I’m such a clutz. Hang on, I’m going to go grab more towels.”

Dean continued to stare at the soaked brown mess that was his failed hopes and dreams as you ran out of the room. How had it all gone so horribly wrong in such a short amount of time?

“Hey, Dean,” Sam called, and Dean waited for the unavoidable mockery. Instead Sam just looked up from his own sack with a mildly put out expression. “You got the wrong salad.”

Dean decided not to give up. His mistake this time was involving food and inappropriate writing materials. His second attempt was written on actual paper and left next to the same book that had remained remarkably unscathed in the previous day's flood. He left the note face down, not because he was delaying the inevitable, but because he didn’t want Sam to see it and correct his grammar or something.

Where liquid was his first downfall, this attempt met its demise in fire. Literally. You'd discovered an especially interesting incantation and wanted to write it down, so you pulled over the nearest blank paper, which just so happened to be the backside of his note. The moment your pen left the page it burst into flames, sending you jolting backwards before you whipped off your jacket and beat the inferno out. All three of you stared at the smoldering aftermath in shock until you mumbled, “Huh… must have spelled something wrong.”

Attempt number three was made digitally in an effort to circumvent any other natural disasters. He stole your phone and signed you up for the same dating website he used to pick up the occasional wayward, lonely woman. He waited until your phone was back in your possession and sent you a request. Then he just had to wait for the email notification to come through. Soon enough your phone buzzed. And continued buzzing. A lot.

“What the…? Why am I getting emails from a dating website? Wow, that is one forward lesbian.”

Lesbian?

“Oh, but that one's pretty. And has a doctorate in English literature. And here's one who likes hiking. And so does this one. And this one. Ooh, she likes intellectually stimulating conversation and foreign movies. Must love dogs. Too bad Sam's not a woman – he'd clean up on here...” You hummed thoughtfully and tapped at the screen a few more times. Then you set the phone down and went right back to reading.

Dean cleared his throat and tried for nonchalance. “What was all that about?”

“Someone must have accidentally used my email instead of theirs to set up a dating profile and checked the interested in women box. Unfortunately, I still seem to swing pretty straight, so I cancelled the account. Though I did send a message to Dr. English. She said she likes one of my favorite books, so I'm hoping she'll be my new internet friend.”

He must have hit the wrong button, but honestly checking that particular box was habit by now. Okay, so maybe he wasn’t so good with the written word after all. He'd just have to do this the old fashioned way. “So-"

“Guys, I just found a box set of The Lord of the Rings trilogy for next to nothing. Who's up for a marathon?”

Dean slammed his hands on the table and lurched to his feet, too frustrated to think straight. “Really Sam? Really?”

He stormed out of the room, embarrassment now coloring his irritation, but he still heard you ask Sam, “What's wrong with him?”

“Not a fan of hobbits. They give him nightmares.”

Yeah, Sam had to go.


	5. Chapter 5

Dean was decided. Today would be the day – this very morning, this very hour, before his coffee cup was empty, he would ask you out and you would know he was asking you out and Sam would not factor in whatsoever. Dean was prepared. He was primed. He was determined. 

You were nowhere to be seen.

He had wandered the bunker for awhile, sipping his coffee sparingly, because he had vowed after all. Either you were the secret world champion of hide and seek or you were not on the premises at all. Sam didn’t turn up in his search either, and a small, immature part of Dean worried that his brother had snaked him.

He tried not to think about that too much – it made him drink his coffee faster and he was already two thirds of the way through.

Eventually, Dean settled at the kitchen table, assuming at some point you’d have to eat. Patience was a virtue, right? Good things come to those who wait. Everything worth having is worth waiting for. Or working for… clichés are hard.

His coffee was cold.

You were laughing when you walked into the room with Sam on your heels, unaware of Dean's turmoil. Your skin glistened in the fluorescent light. Some loose hair got stuck to your face, and you brushed it away impatiently. Sam's shirt was damp at the neckline, his own hair less controlled than usual. All signs pointed to an early morning run.

“You two disgust me.”

“Nothing a shower won't fix.” You grinned, easy and teasing like you didn't realize how ridiculously attractive you were in your disheveled glory.

“I can’t believe you went _jogging_ with Sasquatch.”

“That sounds like a beef jerky commercial,” you mused, pulling a banana from a bunch on the counter. 

“I thought I knew you.”

“What can I say? I haven't run from anything in weeks. My muscles were itchy.”

Dean knew a little something about itchy muscles. Maybe he should take up jogging. Or Olympic level cold showering.

“You should have come with us,” Sam spoke from behind the spout of his water bottle. “You’ve been looking a little tense lately.”

“I’m fine. Thank you very much for your concern.” Dean glared at Sam in a way he hoped conveyed ‘shut up, you jerk.’ Then he steeled himself because the moment had arrived, and there was still a layer of coffee covering his mug's bottom. “Hey-"

Then you did the unimaginable. You unzipped your jacket enough to pull your arms out and left it hanging from your waist. Your sports bra looked very… athletic, like you might have actually spent some money on it. The fabric even matched your pants, like it was an _outfit_ , so he shouldn’t have been surprised that it was all you wore. But how was he supposed to talk to you when your bellybutton was practically making eye contact with him? 

“Hmm?” You paused as you picked up your banana again, looking up at him quizzically. “Did you need something?”

That cold shower. A cold shower and a backbone.

“He needs a swift kick in the pants,” Sam muttered, expression highly unamused.

“Oh, come on, Sam. You know running isn’t for everyone.” Your smiled turned teasing. “Maybe he'd like a Zumba class better.”

“What the hell is a Zumba?”

Your laugh came from the very center of your being, and you stifled it behind the fruit in your hand. Dean wasn’t sure what the joke was, had the sneaking suspicion that it was at his expense, but couldn't care less at the moment. You were happy. That made a little ball of warmth settle right behind his ribs. Or maybe that was too much tepid coffee.

“Well, I’m going to go take that shower I mentioned. You boys behave.” You had the gall to run your fingers through the hair on top of his head as you passed, and he almost fell over backwards chasing the movement, his eyes closing reflexively at the feeling. 

Only when your hand had left him completely did he recall his primary objective for the morning. “Would you go on a date with me?”

You didn’t reply right away, and he immediately regretted how stupid that sounded. What was he, a prepubescent teenager? He opened his eyes, preparing for damage control, to see Sam watching him far too smugly.

“Yeah, she's gone,” Sam shook his head as Dean glanced over his shoulder to swear at the empty space. “What’s the matter with you? I’ve never seen you have this much trouble asking someone out.”

“It's complicated. She's not just some girl in a bar, Sammy. You’re the one who told me not to screw it up!”

“I meant for you to be careful, not catatonic.”

“Something always gets in the way. It's never the right time.”

“The time isn’t going to get better than this. The world isn’t ending, demons aren’t attacking, and she's literally living with you.”

“She took her shirt off, man! What am I supposed to do with that?”

Sam snorted. “You're pathetic.”

“Yeah, well, you're…” Dean struggled to think of something, but ended up just glaring at his traitorous coffee. “Shut up.”

“You’re blowing this up too much – psyching yourself out. You've been friends for years. You know how to talk to her. Just relax.”

“You relax,” Dean grumbled petulantly, downing his coffee dregs just to spite himself.

“And stop pouting.”

“I’m not pouting. I’m a full grown man. I’m brooding.”

“Whatever you call it, it's annoying. Grow a pair, dude.” Sam exited the kitchen, meaning of course that he got the last word, which was just the cherry on top of the mess Dean's morning had turned into.

His brother had a point, though. He'd known you for years. When you murdered monsters with someone, it shouldn't be so hard to talk to them, right? He'd never had this problem before, not with you. But then he'd never really considered you an option either. You two were never in the same place for long, and his life was hard enough without trying to manage a relationship, let alone one over long distances compounded by the stress of hunting.

Things were different now. He had a home base – a home. You could stay here, hunt with them. No more ships passing in the night. He just had to figure out how to get that first date locked down.

And maybe find out if you had anymore of those matching running outfits.


	6. Chapter 6

“I guess it's about time I hit the road again.”

Dean full-on stopped chewing as he stared at you. You were leaving?

“You're leaving?”

Yes, Sam, good. Saying things out loud was a good idea. Dean began to chew haphazardly so he might say things out loud as well.

“I've been here almost a month. I think that's a few steps past wearing out my welcome.”

“You know your welcome doesn’t have an expiration date with us.”

Dean nodded enthusiastically. Why was there so much food in his mouth?

“Because you two are the sweetest. But I wouldn't feel comfortable taking advantage of you and your Batcave any longer. Besides, a friend asked me to go check something out in Bogota anyway.”

Dean finally managed to swallow but then couldn’t think of anything to say now that his tongue was free. Sam shot him a brief glance.

“You want backup?” Sam asked when Dean just sat there like a CPR dummy. Emphasis on dummy.

“Nah, it sounds like a milk run. Thanks for the offer though. Not to eat and run, but he was actually hoping I could get there ASAP, so I’m gonna take off as soon as I get all my stuff together. Thanks for lunch, and you know, everything else. I'll swing through on my way out for all my sappy goodbyes.”

Dean stared at the sink where you'd just left your dishes. He couldn’t believe after everything he’d completely missed his shot. Who knew when you'd be close enough to warrant another visit?

“Dude,” Sam's tone was reprimanding, and Dean let his forehead fall to the table with a thunk. “Why am I the only one trying to get her to stay?”

“You heard her, Sam,” Dean spoke into the tabletop. “She's moving on. Bogota. Friend with a case.”

A ‘he' friend, if memory serves.

“So what? She could work the case and come back, but she doesn’t realize that's what _you_ want. She thinks she’s imposing.”

“If she wanted to stay she would.”

“If she knew you wanted her to stay she would.”

“She's obviously not interested.” Dean sat up to glare at his brother (and also his back was getting stiff). “She has to have picked up on it by now. Maybe this whole time she’s been pretending so that she doesn’t have to hurt my feelings, and I’m the one who needs to take the hint.”

“I’m pretty sure she has no idea you’ve been trying to make a move.”

“Oh, come on, of course she does. I haven’t exactly been subtle.”

“No, you’ve been a complete freak, and she doesn’t seem to notice.”

“Give it up, Sam.”

“Hey!” Sam was looking over Dean's shoulder, which made his stomach plunge to his feet right before Sam's next words brought it back up into his throat. “Do you know Dean's been trying to ask you out?”

Life works out funny sometimes. After everything he had done to save Sam's life over the years, this was how his brother would die - at Dean’s own hands.

“He was?” You sounded genuinely surprised, and Dean could hear shuffling that indicated you were walking further into the room. A moment later you came into his periphery, duffle slung over your shoulder. “You were?”

“Well, yeah, kind of.” He couldn’t bring himself to look at your face, so his eyes flitted somewhere near your shoulder and then returned to glare at Sam.

“Seriously?” Now you sounded upset, so he did look to see your frustrated expression. “When did I get so bad at this? I swear I used to know what men wanted from me.”

“Wait, you really didn’t know?” 

“No!” Your free hand flew out like you were trying to hit your past self. “Do you think I would have been running around in my sweatpants and laundry day t-shirts if I had any idea?”

Sweatpants? The ones with the tear in the right leg just high enough to be questionably appropriate? You weren’t using those as a tool of seduction?

“See? I told you.” Sam smirked, leaning back in his chair and eyeing Dean smugly.

“Shut up, Sammy.”

The conversation stalled, with Sam looking between you and Dean before finally asking you in exasperation, “So?”

“Um…” You shot Dean a glance and then focused back on Sam. “So what?”

“Are you going to go out with him?”

“Oh! Sure. I mean,” you paused, looking upwards in consideration, “I should probably take care of the thing in Bogota first, but when I get back we could go out.”

“Wait, no, hold on.” Dean stood up, drawing all attention, leaned one hand on the table and pointed the other at you. “You are not going to go out with me because my little brother asked. You’re going to go kick the ass of whatever's in Bogota, and then you'll come back here and I'll ask you out myself.”

“Is that what's going to happen?” You were starting to smile, and it was a fight to keep his expression from mirroring yours.

“Don’t test me. I’ve been working on this for a month.”

“He means years.”

“Sam, remember when I said shut up?”

“I appreciate the thought, however long you’ve had it.” Your smile suddenly seemed a little shy, which was just the most fantastical thing. “This hunt shouldn't take longer than two weeks. So… I'll see you soon?”

“Yeah, okay. But one more thing.” He grabbed onto your duffle's strap right above where your own hand held it and gave a sharp yank. The unexpected tug pulled you forward a step, and he had a short moment to enjoy the look of surprise on your face before he pressed his lips to yours. Just once, firmly with very little movement. Then he let go and straightened, watching you blink about twelve times very quickly. 

You hitched your bag further up your shoulder and nodded with finality. “Maybe one week, then.”

You waved at Sam and strode out the door again with new purpose. Dean smiled after you before sitting back down and smirking into his beer.

“I’ve still got it.”

“You’re a moron.”


	7. Chapter 7

Dean was wound tighter than he could ever remember. Not because of some monster or Sam being in danger or an angel wanting to crawl up his butt and take up residence. No, all those problems could be taken care of with a gun or a blade or his fists. But he wasn’t allowed to physically dispatch the current cause of his anxiety. 

You were having a drink with your douchebag ex-almost-boyfriend.

He couldn’t explain it. He’d thought everything had been going quite well with you. You’d come back from Bogota and taken up permanent residence in the bunker on a trial basis. He’d taken you to dinner and a movie that he’d seen at least half of. You’d gone out multiple times since then, were getting along great, fantastic even, to the point Sam had begun to complain about all the PDA. Now, three months later, the king of the douches called you up, asking to meet, and you agreed without hesitation.

What was Dean supposed to think?

Granted, you’d told him the moment you’d hung up, casually, like you grabbed a drink with your exes all the time. You’d also invited him and Sam along, saying you all hadn’t had a night out in awhile. 

So here he sat, in a booth with Sam, watching you at a tall table across the room while his brother made noises of irritation with increasing frequency the longer Dean ignored him.

You laughed at something his grand highness douchebag said, and Dean felt his control snap.

“I’m gonna go get another.”

“Dude, you still have half a bottle.”

“So when I get back I’ll have a bottle and a half.”

“You just want an excuse to go listen in on her conversation.”

“So?”

“ _So_ , that’s really obnoxious. You should trust her.”

“I trust her. I don’t trust him.”

“You don't even know him.”

“I know the last girl who trusted him wound up in a family way.”

“What does that have to do with anything? It’s not like she’s going to sleep with him.”

“I know that!” He did. At least he was pretty sure he knew it. “But you can’t trust a guy who doesn’t know how to wrap it up right.”

“Would you just be cool? It’s only a drink, and-"

Dean didn’t know if there was more to Sam’s thought or not, because he was already halfway to the bar. Even after he’d been granted his second beer, Dean maintained his position, leaning on a convincingly casual elbow as he gave your table the side eye. Your back happened to be facing him, which meant he got a real good look at your grinning companion. Dean was man enough to admit that this douche could be considered attractive, though his eyes were a little close together. That was probably a recessive gene or something, so if you had his baby it would likely get your eyes and look perfect.

Wait, what?

His next swallow was equal parts beer and air.

“So,” the man stopped grinning like an idiot long enough to look serious, “I actually had something I wanted to talk to you about.”

“Shoot.”

“It’s just… I’m wondering if I jumped into things with Desiree too quickly.”

His baby momma's name was Desiree? What, had he knocked up a stripper?

“Well, like you said, there’s a baby involved, and that kind of thing has a pretty definite time constraint. You owed it to yourself and your child to see if it would work out.”

“That’s the thing: I’m not even sure anymore if I’m the father. I found out she was seeing another guy at the same time as me.”

Didn’t that sound familiar…

“Have you had a paternity test done?”

“No, she says she will if I really want her to, but she’s sure he's mine.”

“You’re having a boy?” Your tone had changed, gotten a little softer and breathier. 

“Yeah, I just… I think I might have made a mistake.” His look was full of meaning, and Dean felt the air he swallowed fighting to come back up with company. This guy was obviously trying to find an in with you, to reopen a road. But he was still using terms like wonder and think and might, so he wasn’t even fully committed to the effort, like he was more interested in simply making sure the option was still there.

You deserved so much better than this. Why were you letting this douche canoe reel you back in?

“That sounds like something you should talk to Desiree about. Even if you aren't interested in a romantic relationship, if she's telling the truth, you're still going to have a baby. I don't know Desiree well enough to comment on her, but I do know you, and you're not going to be able to give up on your son.”

You sounded so… detached. Gentle, sure. Kind, definitely. But also like you didn’t really have a vested interest in the situation, like this baby hadn’t been what knocked you out of your pre-girlfriend position in the first place. 

“What about you?”

“What about me?” Now you sound genuinely confused. “You want me talk to her? Look, you know I'd do just about anything for you, but I'm afraid I’ll have to draw the line at heart-to-hearts with the mother of your child, whom I’ve never met, about said child’s paternity. Besides, that’s definitely a conversation you should have yourself. Sorry to interrupt the gravitas of the moment, but I really gotta pee. I’ll be back in a jiff, and maybe we can practice what you want to say to Desiree?”

Dean scrutinized the guy’s face as you slipped away from the table. He seemed perplexed, almost stunned. Douche was also an idiot. He really should have known he'd need to connect a lot more dots if he was going to make it anywhere. 

Dean rather conveniently chose to ignore that he’d made the same mistake for a month.

Without stopping to think about it, he soon found himself occupying your empty seat with a short, “Hey,” in greeting.

“Hey, man.” This guy was friendly enough, even when obviously caught off guard. “Do we know each other?”

“No.” Dean plunked his elbows on the table and tried not to glare over his beer bottle. “Dean Winchester.”

“Oh.” An impressive range of emotions passed over his face, starting with surprise, then recognition, contemplation, and finally understanding. “I see.”

“What’s that supposed to mean?”

Okay, so he was a little pissy, so what?

“I should have expected it, actually. She used to talk about you all the time.”

“She did?”

“Well, you and your brother, but she always seemed to have more to say about you. From her description, you guys were more legend than man. I would have thought she was exaggerating if the rest of the community didn’t back her up. It’s nice to finally meet you, even if the circumstances are a bit disappointing.”

Dean shook his proffered hand automatically. “They are?”

“Yeah, but that's mostly on me. I should have known she wouldn't have been sitting around while I struggled to get my head out of my ass. Truth be told, I always wondered what she was doing waiting on me when she was so clearly into you.”

“She was?”

“Oh yeah. I mean, we got along well enough, probably would have made a good go at an actual relationship, but I doubt she ever talked about me the way she talked about you.”

“Huh.”

“Oh, hey!” Your bright smile was somewhat unexpected; Dean thought you'd at least be upset at him for interrogating your friend. Not that he'd said a whole lot in the end. “You’ve met my boyfriend.”

Dean almost choked on his panic. Since when was this guy your boyfriend? You hadn’t even seemed to notice that he was hitting on you. Had he missed something in his eavesdropping?

But then Dean saw the other guy nod and felt you lean against his side. He realized you had been addressing the comment across the table, which meant he, Dean, was the boyfriend you'd been speaking of.

Dean was your boyfriend. 

Awesome. 

“Not to run out on you, but I just got a text from Desiree. I think I’m going to take your advice and have a long talk with her.”

“Are you sure you don't want to practice a few times?” you offered, but the guy was already slipping back into his jacket. 

“Yeah, thanks though. This all really helped.”

“Glad to be of service. Let me know how it goes.”

And with that, your ex-douche was gone again. Dean let all his tension out on a sigh, then turned his attention back to you as you claimed the newly vacated seat. “So I’m your boyfriend, huh?”

“I thought you were.” Now your brow pinched with concern. “Are you not? Should I not have introduced you that way?”

“No, boyfriend is fine. Saved me the time of telling him to stay away from my girl.”

“Why would you do that? He just wanted some advice. Not a lot to worry about.”

Dean stared in disbelief at your sincere confusion. “Seriously? He called you here to get you back.”

“We were literally having a conversation about his relationship with someone else.”

“No, _you_ were having a conversation about his relationship. _He_ was having a conversation about how he made a mistake leaving you for her.”

“Really? Wow, it’s a good thing I’ve got you. I’m apparently never going to be able to tell when a man is interested in me again.”

“So, what, I’m only your boyfriend because reading social cues is too hard?”

“Among other reasons. Hey, where’s Sam?”

“That better not be your way of saying getting at sasquatch is one of those other reasons.” But he turned anyway to look at the booth where he’d left his brother. A booth that was now occupied with a leggy brunette who appeared extremely interested in everything Sam was saying.

“That’s Dr. English!” Your face lit with excitement. “I told her we were going to be here tonight, but she didn’t know if she could make it.”

“You invited your lesbian love connection from the dating website?” Dean never had confessed to being behind that. Now he had a whole new concern, because not only were you agreeing to meet up with ex-love interests but also potential new ones. He hadn’t realized he’d have to contend with another sex as well.

“After I explained the mix-up she was really understanding. We got onto the subject of our favorite books, and we’ve been chatting ever since. Turns out she’s bi, so I thought I’d do a little matchmaking. Looks like I have pretty good insight into other people's relationships, at least.”

Sam caught the two of you staring, so you gave him a very encouraging thumbs up. He grinned and turned back to his date. Satisfied, you looked Dean to find him already staring at you. “What?”

“So you’re not giving what’s-his-name another shot?”

“Of course not. I’ve been told I never liked him that much to begin with.”

“And you’re not running off with a well-read lesbian?”

“Bisexual, and no, she’s all Sam's.”

“Is there anyone else I need to worry about?”

“Well, there is this one guy. He’s got really nice arms and a pretty face and the coolest car. I’ve had a crush on him for years, and he finally asked me out a few months ago.”

You were smiling and Dean was smiling, and you were pretty sure you were both idiots, but after all isn’t that what love is? Being idiots together? Okay, maybe not, but this was pretty darn good anyway.

“All it takes is a face and a car, huh?”

“Don’t forget the arms. And that’s just the icing on a really delicious cake.”

Dean reached across the table to take hold of your hand. “Wanna catch a movie on Friday?”

“Yes.”

“Want to have dinner on Saturday?”

“Very much.”

“Breakfast on Sunday?”

“Sounds perfect.”

“Wanna double with Sam and his doctor, binge watch Netflix, get our own motel room on hunts, and generally be the obnoxiously adorable couple everyone else hates?”

Any suspicion that you were an emotional wasteland was completely eradicated by the warmth in your chest and the fluttering in your stomach. Dean’s hand was warm on yours, and his eyes were bright and kind and made you feel important. You were probably in love with him. You’d probably been in love with him for years. How about that?

You leaned your elbows on the table, waiting for him to mirror you so you could kiss him. When you pulled back he was still looking at you like you were his favorite thing in the world, so even though the answer to his question seemed obvious, you decided with your past track record, better safe than sorry.

“Absolutely.”


End file.
